Write a Holiday Letter to Your Future Self

building outlined with white christmas lights with a bare tree in the foreground decorated with gold ornaments
Dad, you taught me everything I know about exterior illumination.
— Clark Griswald

A few years ago I started a tradition of writing a letter to my future self after the holidays. I started this tradition after ending a particularly exhausting holiday season, and feeling like something had to change next year.

I noticed that at the beginning of each holiday season I started with love and happiness and loads of energy. I wanted to do all the things and make all the memories possible. 

And yet, despite these bright beginnings, the holidays were reliably turning into a dreaded occasion each year instead of an enjoyable one.

Enter, writing a letter each year to my future self.  

I realized that the problem was not the holidays.  The problem originated in what I expected from the holidays, others and mostly, myself. It seemed as if I had a very poor ability to remember what worked for me and what didn’t from year to year. 

Timing matters with the holiday letter. So,while that year’s holiday remained fresh in my memory, I wrote down what I loved about the holiday and what I would choose to change the following year. 

The first year I did this, I sealed it into an envelope addressed to me, and tucked it into our Christmas ornaments to be rediscovered and read the next year.  

It worked like a charm. The following year I pulled out my letter from what seemed like eons ago. Had it really been only a year since the last round of endless gift buying, late-night cookie baking and holiday exterior lighting plans? I could hardly remember any of it as I excitedly approached a new starting line.

The letter to myself was kind but firm. Cheerful but also realistic.  I appreciated the concise advice and perspective from my past self. 

“Do not do any more cookie exchanges. It’s okay to not spend a ton of time on stockings. Get the neighbor gifts early. Try to gift experiences instead of things. Don’t do the Nutcracker again, it’s way too long. Let people be themselves. You loved having a little tree in your bedroom. Always get the family game. It’s fun every time.”  

The letters serve as yearly reminders of what was worth the effort, what you love no matter what, where the potholes are during the holiday months, and what types of expectations tend to get your tinsel in a tangle  each year. 

You may think you will remember these things next time. You will not.  

These days, I write up my holiday letter in my Google Docs. Then, I put a reminder in my calendar right before Thanksgiving to read my holiday letter for that year. 

Now is a great time to write your own holiday letter. Take out a piece of paper and  pen, or open up your computer. 

Here are some questions to get you started:

What worked really well this season? 

What did you learn about yourself this holiday season? 

What do you want to remember? 

What would you like to give yourself permission to let go of? 

What was totally NOT worth it. 

What do you want to be SURE to do again next year?”

Make a list of things you want to have ready, purchase, or want as reminders for the year. 

Writing a holiday letter might be one of the most thoughtful gifts you receive next year. I get a chuckle each year when I read what I wrote last year. 

 It’s a lovely thing to read caring messages from your past self. 

You Got This,

Kate

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The Gift of Baby Drama